A beach at sunset with birds flying and a person walking.

Oldsmar Vacation Rentals

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Our top choices for Oldsmar vacation rentals

Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,652 reviews)
"This was the perfect place for our beach getaway!"
United States
Christi
The price is CA $265
CA $340 total
includes taxes & fees
Jul 20 - Jul 21
Sunset Vistas Two Bedroom Beachfront Suites

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,207 reviews)
"Clean room and good location"
United States
Sagita
The price is CA $274
CA $358 total
includes taxes & fees
Aug 5 - Aug 6
FUSION Resort Waterfront Suites

Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,108 reviews)
"Great views! Also enjoyed the food and drinks at the poolside bar."
United States
Dana
The price is CA $130
CA $173 total
includes taxes & fees
Jul 19 - Jul 20
Sailport Waterfront Suites

Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (883 reviews)
"First family beach trip in years and this place is exactly what we were looking for !"
United States
Loriedawn
The price is CA $380
CA $711 total
includes taxes & fees
Jul 9 - Jul 10
Surf Beach Treasure Island Resort

Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa
4.0 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (885 reviews)
"Super clean, very nice place to stay five stars"
United States
Carmelino
The price is CA $138
CA $156 total
includes taxes & fees
Jul 20 - Jul 21
Mint House St. Petersburg Downtown by Kasa

Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (748 reviews)
"Excellent accommodations for the price point"
United States
Yvette
The price is CA $185
CA $263 total
includes taxes & fees
Aug 6 - Aug 7
Beso Del Sol Resort

The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (565 reviews)
"Love the small feel and right on the beach"
United States
Danielle
The price is CA $330
CA $429 total
includes taxes & fees
Jul 12 - Jul 13
The Avalon Club

South Beach Oceanfront Resort

South Beach Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1,152 reviews)
"Everything you need and want for a nice relaxing or adventurous beach vacation"
United States
Mitchell
The price is CA $267
CA $507 total
includes taxes & fees
Jul 8 - Jul 9
South Beach Oceanfront Resort

Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (987 reviews)
"The apartment is in good condition overall for the price. Great location right across the beach and close to restaurants. Great resort overall!"
United States
Luis
The price is CA $212
CA $260 total
includes taxes & fees
Jul 12 - Jul 13
Barefoot Beach Resort

John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (385 reviews)
"Love this place one of my favorite hotels!"
United States
angela
The price is CA $120
CA $159 total
includes taxes & fees
Aug 2 - Aug 3
John's Pass Hotel

The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (996 reviews)
"Our stay here was great! The room was very clean and spacious, easy check in, parking, and great location. Highly recommend staying here if visiting Indian rocks beach!"
United States
Jon
The price is CA $225
CA $295 total
includes taxes & fees
Jul 20 - Jul 21
The Fold Hotels Indian Shores

Westwinds Waterfront Resort

Westwinds Waterfront Resort
3.0 star property
Treasure Island
9.0 out of 10, Wonderful, (720 reviews)
"The room was spacious and clean with a great view of the water. The location is great. Enjoyed my stay!"
United States
Karen
The price is CA $235
CA $473 total
includes taxes & fees
Jul 22 - Jul 23
Westwinds Waterfront Resort

Great for Digital Nomads! Spacious Home in Largo

Great for Digital Nomads! Spacious Home in Largo
3.0 star property
Walsingham
The price is CA $290
CA $818 total
includes taxes & fees
Jul 12 - Jul 13
Great for Digital Nomads! Spacious Home in Largo

Swann Avenue Central Tampa Homes

Swann Avenue Central Tampa Homes
2.0 star property
SoHo
5.0 out of 10, (2 reviews)
"Terrible Decision – Do Not Recommend We booked this Studio for 3 nights but only stayed for one. A strong, overwhelming mildew odor filled the unit and actually made us feel physically ill. We also noticed significant water buildup on the toilet seat and cover, which we believe was contributing to the persistent mildew smell. The listing photos are very misleading — they clearly don’t reflect the current condition and appear to have been taken many years ago. In reality, the property is quite...
United States
Donnell
The price is CA $106
CA $377 total
includes taxes & fees
Jul 9 - Jul 10
Swann Avenue Central Tampa Homes

Heated Pool Home Pool Table Spacious Family

Heated Pool Home Pool Table Spacious Family
2.0 star property
Largo
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great "
United States
Oderay
The price is CA $847
CA $1,415 total
includes taxes & fees
Jul 31 - Aug 1
Heated Pool Home Pool Table Spacious Family

The Westshore by Stylish Stays

The Westshore by Stylish Stays
3.5 star property
Beach Park
8.4 out of 10, Very good, (5 reviews)
"This property leaves a lot be desired. please see what was shared with property management. Foul smell of mold and smoking was present towels were unclean communication was thru email only Bathrooms showed it age and lack of cleanliness. This is aged and run down apartment unit dressed up to hide the short coming."
United States
Pedros
The price is CA $102
CA $293 total
includes taxes & fees
Jul 8 - Jul 9
The Westshore by Stylish Stays

St Louis Escape

St Louis Escape
2.0 star property
Old West Tampa
St Louis Escape

Waterfront Resort Condo Gulf Sun Set

Waterfront Resort Condo Gulf Sun Set
3.0 star property
Dunedin
10.0 out of 10, Exceptional, (3 reviews)
"The place was nice quiet and clean. Nice little tiki bar on site also. Good communication before arrival also. "
United States
joe
Waterfront Resort Condo Gulf Sun Set

Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites
3.5 star property
Treasure Island
9.4 out of 10, Exceptional, (655 reviews)
"The room was very clean and had an array of amenities. The beach view was perfect and the staff were very helpful. Our family thought it would be a place to visit again."
United States
Ronnie
The price is CA $270
CA $337 total
includes taxes & fees
Aug 4 - Aug 5
Provident Oceana Beachfront Suites

St Conrad Bungalow House

St Conrad Bungalow House
2.0 star property
MacFarlane Park
The price is CA $69
CA $248 total
includes taxes & fees
Jul 14 - Jul 15
St Conrad Bungalow House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oldsmar Hotel Reviews

Find out more about Oldsmar

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oldsmar. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Oldsmar?

Yes, we have vacation rentals where you'll be just 14.9 mi (23.9 km) from Busch Gardens Tampa Bay, giving you a secluded option to escape the hustle and bustle. Visitors like the top-notch restaurants and beaches in Oldsmar. Make sure you have time to check out the theme park and cafes during your trip.

What are some of the best vacation home rentals in Oldsmar?

The Gemma by Brightwild: You might want to consider this vacation rental near Oldsmar, which is located on the beach and has an outdoor pool, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. It offers a terrace, a private yard, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Oldsmar?

Expedia has 9 vacation rentals for your stay in Oldsmar.

What can I see and do in Oldsmar?

Explore the area and family-friendly sights such as Busch Gardens Tampa Bay, or get out into nature at a spot like Tampa Bay. In the larger area, you’ll find popular places like Raymond James Stadium and Port of Tampa.

What are vacation rentals like in Oldsmar?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Oldsmar. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.